Dimethylformamide → HCID 22463576, compound

HRID 1937255Notes

Reaction equation

HRID 1937255 reaction equation
[C:1]12([OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([OH:11])([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:13][N:14]([CH:16]=[O:17])C>N1C=CC=CC=1>[CH3:13][NH:14][C:16]([O:12][C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([OH:11])([CH2:4]3)[CH2:2]1)[CH2:8]2)=[O:17]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 5738291,3-Adamantanediol2×

Product 1

HCID 22463576HCID 22463576, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Conditions

Temperature
60 °C

Procedure

In an atmosphere of nitrogen, 10 mmole of 1,3-adamantanediol and one drop of pyridine were dissolved in 10 mL of DMF. To the mixture, 20 mmole of methylisocyanato was added dropwise with stirring. Cooling of the resultant mixture with ice was started at about the time exothermic reaction began. When the exothermic reaction is completed, the mixture was heated to 60° C. and then stirred for one hour. As a result, the conversion of 1,3-adamantanediol was 99% and 1-(N-methylcarbamoyloxy)-3-adamantanol (yield 90%) was formed.

Workup

  1. additionTo the mixture, 20 mmole of methylisocyanato was added dropwise
  2. customwas started at about the time exothermic reaction
  3. customWhen the exothermic reaction
  4. stirringstirred for one hour

Sources & evidence

ORD record
ord-3b8437dee00c4a8ba72ba550d2f7dfb0
Source dataset
uspto-grants-2002_05
Patent number
US06392104B1

Reaction notes

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